I wanted to share this story of mine if you are craving some experienced sexy matures in the workplace that are professionals by day and kinky sluts at night! Call it my naughty workplace adventure. It is my belief that there are many MILF Humiliation lovers all over the world and I am one of them. I work in a high-end real estate environment. It is always a high-pressure work environment coupled with long hours. I do encounter a lot of interesting and unique stuff while I work and get hit on by both men and women.
I am heterosexual, but I did some experimenting with sex in college. Of course, this has nothing to do with my job. It’s not like we filmed any gay orgies and bisexual group sex sessions. For the majority of us, this sexual activity happens only in porn movies. And we certainly didn’t do anything like that at work. However, I experienced something that changed my life completely. I will write about that now and hope you enjoy the read.
MILF Humiliation
Work was okay for the most part, with one exception. We had a female boss in her forties. Mrs. Bailey looked fit and slim, but she was terrible for us as a leader. Because of this, my job was exhausting. Employee morale was at an all-time low and most of us were totally spent after work. What made things worse is that management didn’t seem to care at all. Most of the employees were cool and we talked about everyday things to help get us through the day.
Before I forget, my name is Blaine and I’m what most consider to be a handsome man. I’m in my thirties, thirty-one to be exact, and I am very sexually active. I have been with many girls in my life, but have never been with a much older lady. I wanted to have sex with MILF, this was my current fantasy. My previous fantasy and subsequent reality had always been fucking the cum out of barely legal teen pussy. I tried to fuck as much as possible in my twenties. During my working hours, I had sex when I went out for lunch.
I always had several girlfriends (friends with benefits) all over the city. It was pretty exhausting to go to my girlfriend’s place, fuck her roughly, and then go back to work. Damn, did I just write that? After years and years of sexual relationships with many girls, I felt that I needed to change something. For some reason, I wasn’t feeling any sexual pleasure when I fucked all of them. It wasn’t exciting at all at that concerned me. I thought that I needed something completely different than regular sex.
MILF Humiliation – Male Slave
One day, during my break, I decided to read some personal hookup ads online. I had recently purchased a Roku streaming device for my condo. This video on demand (VOD) technology opened a whole new deviant world for me. In searching through the incredible number of MILF Porn channels, I found several very interesting kinky sites available to download. I discovered many women were looking for sex slaves. And I mean all kinds of deviant things; whipping, spanking, ball torturing. This idea made me really horny, and I started to rub my bulge discreetly in the breakroom.
Or so I thought. While I touched myself, my bossy MILF Mrs. Bailey saw me and left the room with supposed disgust. Before she made it halfway down the hall, she called, “Come to my office, I want to talk to you,” she said in an angry tone. I knew I fucked up something bad. “Goodbye, we don’t need you anymore,” ran through my head. I was exhausted, my shift lasted more than fifteen hours, and I looked like crap. I didn’t have time to wash, I was sweaty, and I had the smell of a real man.
As soon as I stepped into her office, I noticed that she was angry with me and I was going to get fired. Mrs. Bailey was standing by the desk, and I noticed how sexy she looked for the first time in my life. Her hair was dark, she was wearing glasses, and had a skirt up to the knees. Her ankles were so sexy. I noticed that her legs are tight and very hot too. Mrs. Bailey was wearing seductive stockings underneath her dress which only added to the intrigue. Suddenly, I felt very horny and worried at the same time.
MILF Humiliation – Submissive Male
Mrs. Bailey unleashed the following tirade; “You did something wrong, and I have to punish you for that. This is not acceptable, I won’t tolerate this behavior. I am the perfect boss, and this mistake is something I can’t have in my office. I will punish you to set an example for the rest. I’ve had many younger guys in my office who did something wrong too. I punished them just like I’m going to punish you.”
Stunned, all I could offer was; “I will do anything to make things right,” I said with fake tears in my eyes. I explained that I needed this job real bad, that I help my family to survive and pay bills every month. “Get down on your knees you loser,” she ordered. I obeyed immediately. Now, the tears weren’t quite so fake. Mrs. Bailey had some strange smile underneath her lips.
From that day, I became her bitch. I did everything she told me, both sexually and non-sexually. When my cell phone buzzed, I knew I had to be in her office immediately. I closed the door so that no one would disturb us. Typically, Mrs. Bailey was sitting in her office chair with legs on the table. I got down on my knees and crawled over to her MILF pussy. She made me lick her juicy cunt (as she called it) for hours.
MILF Humiliation – Slave Domination
My tongue went numb, but she didn’t care. When I didn’t have enough energy, she would throw me on the floor, and sit on my face with her pussy right in my nose. I liked the smell of her juicy muff. I licked her until she came multiple times. On several occasions, I came in my pants without any external stimulation. It was unbelievable. Several months after our special relationship started, the office received news that Mrs. Bailey was being transferred and would no longer work there.
I was despondent when I heard the news. It appeared my MILF Humiliation days were numbered. Perhaps, gone forever. My grief was short-lived as Mrs. Baily informed the group she would be interviewing candidates and taking one of her key employees to the new job site. I can’t express my happiness when an inter-office memo was sent announcing that I was the chosen employee.
I was thrilled! Mrs. Bailey sent me a text congratulating me for being a perfect slave for her. I was totally submissive and always did what she wanted. Nobody had ever made her feel like me. She further confided that she loves me and will forever be my Dominatrix. I am still with her, of course. She is waiting for me to lick her asshole and give her an anal orgasm as soon as I finish writing this story. You can only imagine how sexy she looks while she lays on the bed naked while I fuck her for hours and hours. I can’t wait for more MILF Humiliation!
